The best walks and hikes around Penn
4.6
(1820)
12,882
hikers
82
hikes
Hiking around Penn takes place in the Chiltern Hills, an area characterized by a mix of dense woodlands and open meadows. The landscape provides a varied experience, with routes that traverse both shaded forest paths and sunlit clearings. The region's network of trails offers a quiet setting for walking through the English countryside.
Best hiking trails around Penn
- The most popular hiking route is Penn Wood loop — Chiltern Hills, a 5.6 mile (9.0 km) trail that takes about…
Last updated: May 2, 2026
4.6
(15)
27
hikers
8.98km
02:25
110m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(5)
51
hikers
10.3km
02:46
120m
120m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
Sign up for free
5.0
(4)
54
hikers
10.1km
02:42
110m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.9
(8)
46
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.3
(6)
21
hikers
6.84km
01:51
90m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Tips from the Community
Winchmore Hill goes back to the 12th century: there used to be a small settlement here supporting farms grouped around a Common and a pond (those were the days). In 1958, the pond was filled in, but luckily the Common is still here, on the edge of what used to be Wycombe Heath: 4,000 acres of open common land providing grazing for animals and material for firewood. It's a lovely hamlet. There is a great information board, from which you can learn more about the history of the place. And a good pub in a village can never be wrong! - so make sure you make a stop at The Plough!
1
0
This here is one of the entrances to the beautiful Penn Wood. It's a truly spectacular bit of woodland: dense, green, with lovely paths to run on. Some trees are ancient: one, thought to be the oldest in the wood, is the Holey Oak (there is a hole in the trunk...), and the other is the Penn Pollard, memorable for its very open crown. You're in for a treat here!
1
0
This church was founded over 800 years ago. A number of elements in the church are very old (e.g., the nave is from the 12th century), but the Chapel was rebuilt in the 18th century. Of particular note is the "Penn Doom", one of just five surviving wooden tympanums in the UK. ("Tympanum" is the space between the round arch and the lintel over a doorway, found in many churches.) If you are one for churches, this one is a definite must, and if not... well, one's gotta start sometime!
1
0
A network of footpaths will lead you through the sensational ancient woodland of Penn Wood. The woods are dominated by beautiful oak, beech, ash, and cherry trees with an understory of bluebells, wood anemones, and other wildflowers.
2
0
Penn Wood is a large, ancient woodland situated in the Chiltern Hills not too far from Amersham. The woods are beautiful to stroll around any time of the year, however, if visiting in the spring months, you'll be afforded a beautiful display of seasonal bluebells.
1
0
Frequently Asked Questions
How can I get to hiking trails from the University of Pennsylvania using public transport?
Yes, several great hiking spots are accessible via public transport. For Wissahickon Valley Park, you can take SEPTA Regional Rail. To reach the John Heinz National Wildlife Refuge, you can use a combination of SEPTA services. The Schuylkill River Trail is very accessible, with parts of it running right through the city near campus.
Are there any dog-friendly hiking trails near Philadelphia?
Many parks in the Philadelphia area welcome leashed dogs. Wissahickon Valley Park is a popular choice with its extensive trail network. Valley Forge National Historical Park also allows dogs on its trails, offering a mix of history and nature for you and your pet to explore.
Where can I find hikes with waterfalls near Philadelphia?
For impressive waterfalls, you'll need to take a day trip. Ricketts Glen State Park, about a 2.5 to 3-hour drive, is famous for its Falls Trail, which passes by more than 20 waterfalls. A closer option is Hickory Run State Park, about 90 minutes away, which features the scenic Hawk Falls.
What are some easy, beginner-friendly hikes accessible from West Philadelphia?
The John Heinz National Wildlife Refuge offers over 10 miles of flat and easy trails, like the 3.5-mile Wetland Loop, perfect for beginners and birdwatching. Another excellent option is the main path in Wissahickon Valley Park, known as Forbidden Drive, which is a wide, level gravel trail that follows the creek.
What is the terrain like in Wissahickon Valley Park?
Wissahickon offers a variety of terrains. The main trail, Forbidden Drive, is a wide, flat gravel path suitable for all skill levels. For a more challenging hike, the upper trails on the valley sides are rugged, rocky, and steep in sections, providing a true wilderness feel within the city.
Are there any good circular walks or loop trails in the area?
Yes, you can find great loop trails nearby. Valley Forge National Historical Park has the 6.6-mile Joseph Plumb Martin Trail, which is a paved loop connecting key historical sites. For a more rugged experience, Ricketts Glen State Park's 7.2-mile Falls Trail is a challenging but rewarding loop renowned for its scenery.
What's the best time of year to hike around Philadelphia?
Spring and fall are ideal for hiking in the Philadelphia region, offering pleasant temperatures and beautiful natural scenery like spring wildflowers and autumn foliage. Summer can be hot and humid, so early morning hikes are best. Winter hiking can be rewarding, but be prepared for cold, ice, and snow on the trails.
Are there any hiking clubs or groups at the University of Pennsylvania?
Yes, students can join the Penn Adventure program, which organizes a variety of outdoor trips. They offer guided day hikes to local spots as well as longer backpacking and camping excursions to more distant locations, which is a great way to explore the outdoors with a group.
What should I wear for a hike in a place like Wissahickon Valley Park?
For the flat Forbidden Drive, comfortable walking shoes are sufficient. If you plan to explore the steeper, rockier side trails, proper hiking shoes or boots with good grip are essential. It's also wise to wear layers, as the shaded gorge can be cooler, and always check the weather forecast before you go.
Where can I find a challenging day hike from Philadelphia?
For a strenuous hike with rewarding views, consider a day trip to the Delaware Water Gap National Recreation Area, about two hours away. The hike to the summit of Mount Minsi on the Appalachian Trail involves a significant climb and offers fantastic views over the river and into New Jersey.
What are some good options for family-friendly trails?
The Schuylkill River Trail is an excellent choice for families, offering a paved, flat path perfect for walking or biking, including the scenic Schuylkill Banks Boardwalk. Morris Arboretum & Gardens, affiliated with Penn, also provides a wonderful family outing with its easy, winding paths through beautiful gardens.
Most popular attractions around Penn
Get inspired with the komoot mobile app
Explore more
Browse the best Hikes in other regions.
